The five founding partners were: Tony Hamblin, Prem Watsa, Roger Lace, Brian Bradstreet and Frances Burke.

From 1985 to the end of 2010, the firm had a compound growth rate of approximately 25% in book value per share (per year), it is about 243 times what Fairfax began with in 1985.

[citation needed] As early as the 2003, in an annual report issued by the company, chief executive Prem Watsa raised concerns about securitized products and talks about the subprime mortgage crisis and the United States housing bubble.

As of September 30, 2007, Fairfax and its subsidiaries owned an enormous credit default swap (CDS) book with a $18.5 billion notional amount and an average term to expiry of 4.2 years, on about 25 to 30 companies, the majority of which were bond insurers and mortgage lenders.

[13] The deal was later scrapped in favor of a US$1 billion cash injection which, according to one analyst, represented the level of confidence BlackBerry's largest shareholder had in the company.

[14] In 2016, Fairfax offered seed funding to Kitchener startup, DOZR Inc. through their investment and innovation unit, Fair Ventures.

Based in Miami, Florida, it offers a wide range of general insurance products, including property, automobile and various specialty lines, through its subsidiaries located in Argentina, Chile, Colombia and Uruguay.

[citation needed] On August 9, 2022, Fairfax Financial proposed a $954 million takeover bid for the Canadian restaurant operator Recipe Unlimited Corp.[19]